


One Shots

by Bloodcountessbathory



Category: Pokemon GO
Genre: F/M, One Shot, Team GO Rocket (Pokemon), Team rocket leader Cliff
Language: English
Status: In-Progress
Published: 2021-02-14
Updated: 2021-02-27
Packaged: 2021-03-14 10:08:41
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,094
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29416908
Author URL: https://archiveofourown.org/users/Bloodcountessbathory/pseuds/Bloodcountessbathory
Summary: This is a series of little reader insert one shot ideas I've had for Cliff x Reader. Each chapter will be it's own little story. Thanks for reading!
Relationships: Cliff (Pokemon Go) x Reader
Kudos: 4





	1. Valentine's Day

You had stalled in the break room until you were sure most of your fellow Grunts would be gone for the day before making your way to the locker room to change. As you opened the door two other girls were just coming out and you forced a smile and wave as they left before quickly dropping the cheery act as you headed to your locker. It was Valentine’s Day and you hadn’t intended to spend it alone, in fact, you still had reservations for later this evening for you and...No, you thought, you weren’t even going to think his name. He didn’t deserve it. Even though you hadn’t been together long, breaking up on today of all days was low. You yanked open your locker as you fought back tears, thankful that no one else was around to see you like this. Glancing at the small mirror in your locker you tried to push thoughts of him away but instead your reflection began to blur. You angrily swiped the tears out of your eyes with one hand while the other balled into a fist at your side, and you almost gave in to the strong urge to slam your fist into your locker. Instead an idea sparked in your mind and you grabbed a pair of leggings and tank top from your locker.

You slowly pushed open the door to the in-house gym, wincing as it creaked, and listened for signs of anyone else. Not hearing anything you stepped in and made sure the door shut gently behind you. It felt silly, sneaking into somewhere you had every right to be, but you really didn’t feel like running into anyone right now. You made your way over to the piece of equipment that had sparked this idea in the first place, the punching bag. Dropping your water bottle and towel next to it you popped in headphones, confident that if no one was here now there wouldn’t be anyone later given what day it was. It didn’t take long, especially as you pictured your newly ex-boyfriend’s face on the bag, to get in a zone and work up a sweat.

Cliff pushed back from his desk with a loud sigh, the last report of the day was finally finished and it was about time. He was the last one here, Sierra and Arlo had taken off early citing the holiday but Cliff didn’t have plans and figured he’d rather not let this work pile up for the next day. Standing up with a stretch he checked the time and was surprised to see it wasn’t as late as he had thought. Maybe there was some time to get a workout in before it got too late. He shut down his computer before changing in his office and heading down to the gym. As he opened the door he was surprised to hear someone else clearly going to town on the punching bag and was even more surprised to see who it was. You evidently hadn’t seen or heard him as you continued to take some kind of emotion out on the poor bag, something Cliff had to admit he wouldn’t have pictured you ever doing. You had joined Team Rocket a few months ago and had landed on his team. While the two of you had never had much interaction beyond a professional comment on training here and there you had definitely caught Cliff’s attention with your skill. And looks. Cliff thought as he found himself staring at you but quickly brushed the thoughts away. He was your boss after all, and he had heard you were dating someone anyway. Not wanting to startle you he cleared his throat to try and get your attention but was unsuccessful so he moved forward a few feet to try again. As he did you let out a shout and gave the bag a kick that sent it swinging right to where he had moved. He caught the bag with both hands as your hands flew to your face.

“Oh, I’m so sorry!” You exclaimed as you yanked your headphones out. “I didn’t know anyone was still here.” _Shit. Shit. Shit._ Why was he still here?!

“No worries. No harm done, although I don’t know if the same can be said for the bag.” He joked before catching the look on your face. Were those tears? He frowned. “Everything alright?”

“Yeah, mhmm, all good here.” You tried smiling. “Just...um…” _No, no, no, no, no!_ You mentally yelled at yourself as the adrenaline began to wear off. You were pretty sure all the anger at your ex had been taken out and now all that was left was the hurt. But dammit, you weren’t going to cry in front of the boss! “Actually I was just leaving.” You bent down and grabbed your stuff intending to make a hasty retreat to the locker room but a warm hand on your shoulder stopped you.

“Are you sure you’re okay?” Cliff’s tone was gentle and sincere and you couldn’t stop the stream of hot tears that escaped your eyes this time. “Hey-” He began but you cut him off by standing up abruptly.

“I’m sorry, I shouldn’t be...I should go.”

“(Y/N).” Cliff looked at you with concern. He didn’t like that you were crying and had a sudden urge to know why and fix it. “Hey, you can talk to me, what’s wrong?”

“It’s...stupid.” You laughed at yourself as you brushed your cheeks with the back of your hand.

“If it has you this upset it isn’t stupid.”

You eyed Cliff for a long moment as you contemplated telling him. On one hand he was the boss and your ex was also on his team. On the other hand he did seem genuinely concerned right now. “It’s Steve. We... _he_ just broke up with me.” You finally said, swallowing hard while not daring to look at your boss’s reaction.

“Oh, I’m sorry to hear that.” Cliff had heard that you two were dating and while it wasn’t good that you were upset a small part of him was glad you were now single.

“I told you it was stupid.” You let out a small laugh. Now that you had finally let yourself cry about it you felt better and a little silly. “It’s just...today of all days, ya know? I had reservations and everything...I’m sorry. I shouldn’t be complaining to you.”

“No, it’s fine, really!” Cliff smiled warmly at you and placed a hand on your shoulder, giving it a little squeeze. “My door is always open if you need to talk.”

“Thanks.” You smiled shyly back suddenly very much aware of the fact that you were alone in here with your boss. Your hot boss. You felt your face begin to turn red and knew you should probably leave before you made a fool of yourself again. “Well, I guess I should get going.”

“Are you sure you’re okay?” Now that you had said you were leaving Cliff realized he wanted to find a reason for you not to.

“Yeah, I’m good. Thanks.” You smiled at him again and Cliff’s heart beat a little bit faster in his chest.

“What about your reservations?” He asked as you began to turn away and was glad when you turned back.

“What?” You tilted your head to the side with a laugh.

“You said you had reservations for tonight. It would be a shame for it to go to waste. Why don’t I take you?”

You froze. Did your boss really just ask to take you to dinner?

Cliff took your reaction as a bad sign and tried backpedaling. “I mean, if you want. I would feel terrible letting you go home like this-.”

“Yes.” You interrupted him before you could change your mind. Like he said, it would be a shame if the reservation, not to mention the little red dress hanging in your closet, went to waste. And if you cleaned up quickly you should make it just in time. “That sounds nice.”

“Great. It’s my treat, you deserve it.” Cliff grinned. “For all your hard work, that is.” He added quickly hoping he didn’t sound too unprofessional, reminding himself again he was your boss.

You told him you needed to get cleaned up first and gave him your address to pick you up at in an hour. As soon as you were out of headquarters you began running, thanking Legendaries you didn’t live far. Before you knew it the hour was up and your doorbell was being rung. You took another quick look in the mirror, smoothing your hair one more time before grabbing your keys and opening the door.

To say Cliff was surprised would be an understatement. Aside from in the gym earlier he had only ever seen you in your Grunt uniform and seeing you in a dress, especially a dress like the one you had on, was a pleasant surprise. “Wow, (Y/N), you look stunning.”

“Thanks.” You blushed as you stepped outside. “You don’t look half bad yourself.” Cliff had ditched his Team Rocket uniform for black slacks and a blue button up shirt; that was tight in just the right places you found yourself thinking. He hurried to open the passenger door for you before getting in himself, following your directions to the restaurant.

The table you two were seated at was small and draped in a pink table cloth that was covered in red hearts with a bouquet of roses in the middle. You groaned internally having forgotten that you had chosen this place for the romantic atmosphere they were known for on this holiday.

“Ahh, sorry, I forgot about all this.” You smiled sheepishly.

“Don’t be.” Cliff seemed more amused than anything. “I understand, you weren’t supposed to be here with me.”

“Right…” Your heart sank a bit as he reminded you of what had happened this morning. Seeing your expression Cliff immediately regretted bringing it up.

“I’m sorry, (Y/N), I shouldn’t have mentioned it.”

“It’s okay.” You forced a smile and reached for your glass but were startled when Cliff placed his hand over yours.

“If it’s any consolation I think he’s an idiot. Any guy would be lucky to be here with you, (Y/N).” You met gazes across the table but you were fortunately saved from coming up with a response as the food arrived.

For the rest of the meal you avoided any mention of your ex and the obvious romantic setting this was supposed to be, soon forgetting about all that completely. Cliff was the perfect gentleman throughout and by the time the check came you were totally at ease and genuinely sad that you would be going home. It had actually been nice talking with him, he wasn’t all Team Rocket and protein powder like everyone assumed. And every time he smiled or laughed you felt a little flutter in your stomach.

“Thank you, I had a great time. I needed this.” Your sentiment was genuine but your smile was nervous as Cliff walked you to your door, he had insisted on it even after you pointed out it was only a few feet from the curb he was parked at.

“I’m glad. You deserved it.” Cliff surprised you, and himself, by reaching out to tuck a strand of your hair behind your ear. Realizing what he did he quickly pulled his hand back. “I’m sorry, I shouldn’t have-”

You cut off his apology by leaning up to kiss him. Maybe it was the day or the mood or the wine, not that you had had that much, or the way he had been smiling at you but in that moment you had just felt like it was the right thing to do. Your risk paid off when you felt his strong arm wrap around your waist and pull you closer to him. After a few moments you both pulled back.

“Does this mean I’m going to have to quit Team Rocket?” You joked, biting your lip as you looked up into his eyes.

“Quit? No. Change teams, probably.” Cliff smiled again, melting your heart a little more, and brought a hand up to cup your face as his thumb traced a line across your cheek.

“I can live with that.” You laughed before he leaned in to kiss you again. This was definitely a better Valentine’s Day than you had expected.


	2. Rain and Art

You slinked out of Sierra’s office feeling defeated, her shrill berating still ringing in your ears. You had been on Team Rocket for almost a year now and had always done okay. Not great, you thought to yourself, but not this bad. It was just something about the last few weeks that had you off your game. When you had lost to that Trainer earlier you had even contemplated not going back to Headquarters at all. How were you going to explain that you lost because you used a water-type against a grass-type for Mythic’s sake?! That was a rookie move and you knew it and that Sierra was not going to be happy about it.

And it wasn’t just that. Last week you could have sworn Sierra told you to drop those papers off to Giovanni in his office for her but when you did the boss wasn’t there. You had left the door open thinking you were just going to run in and drop them on his desk but somewhere in those few minutes you hadn’t noticed Giovanni’s Persian slink out and well...he wasn’t very happy about that to say the least. You thought for sure you were going to be fired and thankfully you weren’t. You needed this job, at least until you could get your feet on the ground doing what you really wanted to do.

But that was another thing you couldn’t seem to get right either. You had always dreamed of being an artist; of having your work in a gallery, or maybe working for a big time animation company. Even though you had been drawing since you could pick up a pencil it wasn’t until recently you felt confident enough to post some of your work online, but that hadn’t gone well either. Sure a lot of people liked it but for some reason the people that took the time to write mean comments about it stuck in your head. ‘A 3rd grader could do better’, ‘This is awful, why did they even bother to share it’, ‘You suck’. And maybe you did, you thought as the elevator dinged on the ground floor.

You took one look at the weather outside and your mood sunk even more. It was raining, of course it was raining because of course you didn’t have an umbrella. Why would you? Just another thing you’ve gotten wrong today. Fortunately the bus stop was around the corner so it wasn’t too far of a walk to get wet. As you rounded the corner however you were greeted by the backside of said bus pulling away from the stop.

“No, no, no, no!” You ran after it, tucking your backpack to you as best you could to keep it from getting soaked through and ruining your sketchbook within. The bus however did not stop and you were left standing alone in the street, in the rain, and feeling like even more of a failure than you did five minutes ago. You couldn’t tell if it was rain or tears running down your face, but who cared anyway?

“Bad luck, huh?” You turned at the voice and were surprised to see one of the other Team Rocket Leaders, Cliff, standing behind you under a large umbrella.

“Yeah, that’s about it.” Your shoulders sank and you looked down only to be further surprised when Cliff stepped closer so you were under the umbrella as well.

“How long until the next one?”

“Oh, um…” You checked your watch and sighed. “Only another hour.” You tried to sound positive, he was technically one of your bosses and didn't need to listen to your problems. It apparently didn’t come off that way.

“Everything okay?” Cliff frowned at your tone of voice. Were you really that upset over a bus? “An hour isn’t too long, I can wait with you till the next one.”

“Oh, no really, that isn’t necessary!” You began to protest but he stopped you.

“I insist. In fact, there’s a coffee shop around the corner, why don’t we wait there.” There was clearly more going on here than a missed bus and something was tugging at Cliff’s heartstrings saying he needed to find out what. He ignored your objections and placed a firm hand on your back and began steering you up the street while still managing to keep the umbrella over both of you.

A few minutes later and you were inside and out of the rain, which you had to admit was nicer than standing outside alone in it. Cliff insisted on ordering drinks and paying for them, even going as far as to wave you off while he waited for them to be made so you could grab a table. It was rather busy and the only open spot was a small table with no chairs that was pushed in front of the corner of the booth that ran along the wall. You took a seat on one corner of the booth and tried wiping off your outer layers as best you could with the napkins on the table before Cliff walked over with your drinks.

“One hot chocolate.” He smiled, setting the cup down in front of you as he took a seat in the other corner of the booth making you very aware of how small the booth was. Or maybe it was just that he was that big.

“Thanks.” Cliff eyed you as you took a sip. You seemed to have cheered up a bit but there was still a sadness behind your eyes.

“So, everything okay? You seem a bit down if you don’t mind me saying.” You looked up as Cliff’s brows furrowed and he continued. “Is this about boss’s Persian last week?” He, of course, knew all about the incident and the new one you were torn by the boss. And he didn’t want to pry further but your name had also come up quite a few times with Sierra when she was in a bad mood.

“I...guess.” You sighed before muttering. “Just another thing I can’t do right.”

“Hey, it could have happened to anyone…” Cliff began but you interrupted.

“But it didn’t, I made that mistake.” You began as you stared down at your cup still in your hands. “And I keep making mistakes, and using the wrong pokemon, and I’ll never be good at this or anything.” You took a deep breath as the words came flooding out of you as the pent up emotions of the last few weeks pushed their way to the surface and threatened tears in your eyes. “I just...need this job. At least until...oh!” You had been so caught up in getting here you forgot about how wet your bookbag had become and hoped your sketchbook hadn’t been ruined. Diving into your bag you pulled it out and breathed a sigh of relief to find it safe and dry.

“What’s that?” Cliff’s voice brought you back to the moment and you looked up to meet his curious gaze.

“It’s...nothing really. Just a sketchbook. I was worried it might have gotten wet.”

“You draw?”

“Um, a bit.”

“May I see?” You froze, the words ‘3rd grader’ and ‘You suck’ suddenly ringing in your mind again.

“Oh, I don’t know…” While you glanced down at the book in your hands you missed the playful smirk on Cliff’s face but next thing you knew he had reached over and plucked it from your hands. “Hey!” Your eyes went wide in panic as he opened to the first few pages. Most of which were drawings of pokemon.

“Wow, these are really good.”

“Really?” You felt your face flush as he continued flipping through. Cliff was probably the last person in the world you would have ever imagined having any interest in art but here you were. Sharing them with him, your boss. Your tall, muscular, attractive boss.

“Really. Much better than anything I could ever do.”

“Thanks.” You busied yourself by taking another sip of your drink.

“Oh. My. Stars!” Cliff let out a deep, hearty laugh as he turned the book towards you. “It looks just like her when she’s in a mood!”

Your heart pounded in your chest as you saw what he was talking about. You had forgotten those drawings were in there. This one in particular was Sierra towering over a huddled group of Grunts as she wagged a finger at them. You had also purposefully drawn her head three times bigger than her body with an over-exaggerated sneer and her mouth open wide with fangs showing. It was by no means one of your better works and definitely not something you had ever intended to let anyone else see, especially not another Team Rocket Leader!

“No, wait, it’s not…” Cliff ignored you and had already flipped to the next page while still chuckling. This one you actually liked, it was Arlo working over some paperwork at his desk. You were supposed to be filling out reports but had taken a quick moment to pull out your sketchbook and had drawn the whole thing without Arlo even looking up. Which led you to the next page...oh no! You thought and reached for the book but it was too late. The next drawing was of Cliff, you had been on lunch and he was training with some grunts and his smile and laugh…

“Well, well. I think this one is the best.” Cliff smirked. You were very much aware of how flushed your face must be.

“It’s just...I was just...um.” You cast about for an explanation but your mind was blank. Cliff’s expression softened, catching on to how flustered you had become, and he closed the book. He hadn’t meant to cause offense, only to make you smile. You were cute when you smiled, he found himself thinking.

“You’ve got a lot of talent, (Y/N).” He was glad when you looked at him and your eyes were bright, the traces of sadness in them gone. “Seriously, keep it up. You could really go places with this.”

“That’s kind of the idea.” You bit your bottom lip as you slid the sketchbook away.

“And don’t take anything at work too seriously. Everyone makes mistakes sometimes. Don’t beat yourself up over it.”

“Yeah sure, _everyone_. Everyone except you...and Sierra I’m sure.”

“Oh trust me, we’ve made mistakes.” He chuckled, glancing around for a moment before leaning in like he was about to tell you a secret. “This one time when Sierra was just starting out she thought she could battle a Chinchou in a rainstorm. Let me tell you her hair was completely frizzy for at least a week.”

The image of Sierra with anything other than perfect hair sent you into a fit of laughter.

“You can’t ever say that I told you that.” Cliff grinned back at you, placing a finger over his lips and winking. A different kind of flush crept across your face and you looked down at your drink again to avoid eye contact.

“As long as you don’t tell anyone about those drawings.” You said sheepishly, daring a glance up at him through your lashes.

“What drawings?” Cliff faked an oblivious expression which got you both laughing again.

“Thanks.” You said and genuinely meant it. You felt leagues better than you had when you left work, and probably the best you had felt for some weeks. Glancing down at your watch you were dismayed to see the time. “Oh, shoot. Bus should be here any minute. I need to catch that.”

Cliff stood as you gathered your things. He was glad you were leaving in a better mood but a part of him was wishing you didn’t have to leave at all. “Alright, be safe getting home. And, (Y/N), if you ever need anything my door is always open.”

“Thanks again.” You smiled. Suddenly the prospect of going to work tomorrow didn’t seem too bad.


End file.
